4Alpha-bromo-5alpha-cholestan-3beta-ol and nor-5alpha-cholestan-3beta-ol derivatives-stereoselective synthesis and hormonal activity in Caenorhabditis elegans.

We describe the stereoselective synthesis of 4 alpha-bromo-5 alpha-cholestan-3 beta-ol, 21-nor-5 alpha-cholestan-3 beta-ol, 27-nor-5 alpha-cholestan-3 beta-ol and 21,27-bisnor-5 alpha-cholestan-3 beta-ol. In order to clarify the in vivo metabolism of cholesterol, these compounds have been used for feeding experiments in Caenorhabditis elegans. Our preliminary results provide important insights into the metabolism of cholesterol in worms.